9-julolidinyl derivatives and process of preparing them

Abstract

The invention provides processes for the preparation of both known and novel [bis(substituted-aryl) (indolyl)]methanes and [(substituted-aryl) (heteryl) (indolyl)]methanes, useful as color formers, particularly in carbonless duplicating and thermal marking systems, which comprises the interaction of [bis(substituted-aryl) (phenylsulfonyl)]methanes and [(substituted-aryl) (heteryl) (phenylsulfonyl)]methanes with indoles in the presence of either an alkaline or an acidic catalyst.

We claim: 
     
       1. A [(2-R 1  -3-R 2  -4-R 4  -phenyl)(9-julolidinyl)(1-R 9  -2-R 10  -5/6-R 11  -indol-3-yl)]methane having the formula ##STR24## wherein: R 1  represents hydrogen, C 1  to C 3  alkyl, non-tertiary C 1  to C 4  alkoxy, halo or dialkylamino in which alkyl is non-tertiary C 1  to C 4  alkyl; R 2  represents hydrogen or nitro;   R 3  represents hydrogen, C 1  to C 3  alkyl, non-tertiary C 1  to C 4  alkoxy, halo, nitro, dialkylamino or N-alkylbenzylamino in which alkyl is non-tertiary C 1  to C 4  alkyl and benzyl may be substituted in the benzene ring by one or two of halo or alkyl;   R 9  represents hydrogen, C 1  to C 18  alkyl, C 2  to C 4  alkenyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1  to C 3  alkyl;   R 10  represents hydrogen, C 1  to C 3  alkyl, phenyl or ##STR25##  in which B" represents hydrogen, C 1  to C 18  alkyl, C 2  to C 8  alkenyl, benzyl or benzyl substituted in the benzene ring by C 1  to C 12  alkyl, halo or C 1  to C 8  alkoxy; and   R 11  represents one or two of hydrogen, C 1  to C 3  alkyl, C 1  to C 3  alkoxy, halo or nitro.   
     
     
       2. [(4-Dimethylaminophenyl)(9-julolidinyl)(1-ethyl-2-methylindol-3-yl)]methane according to claim 1. 
     
     
       3. A process for preparing a [(X)(Y)(1-R 9  -2-R 10  -5/6-R 11  -indol-3-yl)]methane having the formula ##STR26## which comprises interacting a [(X)(Y)(R-phenylsulfonyl)]methane having the formula ##STR27## with an indole of the formula ##STR28## in the presence of an alkaline or an acid catalyst wherein: X represents a moiety selected from the class having the formulas ##STR29##  in which R 1  represents hydrogen, C 1  to C 3  alkyl, non-tertiary C 1  to C 4  alkoxy, halo or dialkylamino in which alkyl is non-tertiary C 1  to C 4  alkyl, R 2  represents hydrogen or nitro; and   R 3  represents hydrogen, C 1  to C 3  alkyl, non-tertiary C 1  to C 4  alkoxy, halo, nitro, dialkylamino or N-alkylbenzylamino in which alkyl is non-tertiary C 1  to C 4  alkyl and benzyl may be substituted in the benzene ring by one or two of halo or C 1  to C 3  alkyl;   Y represents a moiety selected from the group having the formulas ##STR30##  in which R 4  represents hydrogen, C 1  to C 3  alkyl, non-tertiary C 1  to C 4  alkoxy, halo or dialkylamino in which alkyl is non-tertiary C 1  to C 4  alkyl, R 5  represents hydrogen, C 1  to C 3  alkyl, non-tertiary C 1  to C 4  alkoxy, halo, dialkylamino or N-alkylbenzylamino in which alkyl is a non-tertiary C 1  to C 4  alkyl and benzyl may be substituted in the benzene ring by one or two of halo or C 1  to C 3  alkyl,   R 6  represents hydrogen, non-tertiary C 1  to C 18  alkyl, C 2  to C 4  alkenyl, benzyl or benzyl substituted in the benzene ring by one or two of C 1  to C 3  alkyl or halo,   R 7  represents hydrogen, C 1  to C 3  alkyl or phenyl, and   R 8  represents one or two of hydrogen, C 1  to C 3  alkyl, C 1  to C 3  alkoxy, halo or nitro;   R 9  represents hydrogen, non-tertiary C 1  to C 18  alkyl, C 2  to C 4  alkenyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1  to C 3  alkyl;   R 10  represents hydrogen, C 1  to C 3  alkyl, phenyl or carboxy;   R 11  represents one or two of hydrogen, C 1  to C 3  alkyl, C 1  to C 3  alkoxy, halo or nitro; and   R represents one or two of hydrogen, non-tertiary C 1  to C 12  alkyl, C 1  to C 3  alkoxy, halo, nitro or acetamido.     
     
     
       4. A process according to claim 3 wherein X is ##STR31## and Y is ##STR32## in which R 1 , R 2 , R 3 , R 4  and R 5  each have the same respective meanings given in claim 3. 
     
     
       5. A process according to claim 3 wherein X is ##STR33## and Y is ##STR34## in which R 1 , R 2 , R 3 , R 6 , R 7  and R 8  each have the same respective meanings given in claim 3. 
     
     
       6. A process according to claim 3 wherein X is ##STR35## and Y is ##STR36## in which R 1 , R 2  and R 3  each have the same respective meanings given in claim 3. 
     
     
       7. A process according to claim 3 wherein X is ##STR37## and Y is ##STR38## in which R 6 , R 7  and R 8  each have the same respective meanings given in claim 3.